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Showing metabocard for PIP(18:0/18:3(9Z,12Z,15Z)) (HMDB0009953)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (80) Show 80 proteinsXML
enzymes (80) Show 80 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-12 02:02:36 UTC
Update Date2020-02-26 21:32:47 UTC
HMDB IDHMDB0009953
Secondary Accession Numbers
  • HMDB09953
Metabolite Identification
Common NamePIP(18:0/18:3(9Z,12Z,15Z))
DescriptionPIP(18:0/18:3(9Z,12Z,15Z)) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP(18:0/18:3(9Z,12Z,15Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.
Structure
Data?1582752767
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PIP(18:0/18:3)HMDB
PIP[3'](18:0/18:3(9Z,12Z,15Z))HMDB
1-Octadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)HMDB
Phosphatidylinositol phosphate(18:0/18:3)HMDB
PIP(36:3)HMDB
1-Stearoyl-2-a-linolenoyl-sn-glycero-3-phosphoinositol-phosphateHMDB
1-Octadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphoinositol-phosphateHMDB
Phosphatidylinositol phosphate(36:3)HMDB
PIP(18:0/18:3(9Z,12Z,15Z))Lipid Annotator
{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonateGenerator
Chemical FormulaC45H82O16P2
Average Molecular Weight941.0705
Monoisotopic Molecular Weight940.5078096
IUPAC Name{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1R,5S)-2,3,4,6-tetrahydroxy-5-{[hydroxy(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphoryl]oxy}cyclohexyl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C45H82O16P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)57-35-37(59-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-58-63(55,56)61-45-42(50)40(48)41(49)44(43(45)51)60-62(52,53)54/h6,8,12,14,18,20,37,40-45,48-51H,3-5,7,9-11,13,15-17,19,21-36H2,1-2H3,(H,55,56)(H2,52,53,54)/b8-6-,14-12-,20-18-/t37-,40?,41?,42?,43?,44-,45+/m1/s1
InChI KeyKFWDHEJMINKGBX-CFVBTEIUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentGlycerophosphoinositol phosphates
Alternative Parents
Substituents
  • Glycerophosphoinositol phosphate
  • Diacylglycerophosphoinositol
  • Glycerophosphoinositol
  • Inositol phosphate
  • Cyclohexanol
  • Fatty acid ester
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
logP6.53ALOGPS
logP9.56ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.08ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area256.04 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity243.19 m³·mol⁻¹ChemAxon
Polarizability104.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
  • Brain
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027140
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131750489
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 80 proteins in total.

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Enzymes

Enzyme Details
1. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB1
Uniprot ID:
Q9NQ66
Molecular weight:
138565.805
Enzyme Details
2. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This form has a role in retina signal transduction.
Gene Name:
PLCB4
Uniprot ID:
Q15147
Molecular weight:
136105.065
Enzyme Details
3. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB2
Uniprot ID:
Q00722
Molecular weight:
134023.21
Enzyme Details
4. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB3
Uniprot ID:
Q01970
Molecular weight:
138797.725
Enzyme Details
5. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2
General function:
Involved in phosphoinositide phospholipase C activity
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:
PLCG2
Uniprot ID:
P16885
Molecular weight:
147868.67
Enzyme Details
6. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1
General function:
Involved in calcium ion binding
Specific function:
Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration.
Gene Name:
PLCG1
Uniprot ID:
P19174
Molecular weight:
148658.92
Enzyme Details
7. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. Essential for trophoblast and placental development.
Gene Name:
PLCD1
Uniprot ID:
P51178
Molecular weight:
88134.23
Enzyme Details
8. N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
Enzyme Details
9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
Enzyme Details
10. Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065

Only showing the first 10 proteins. There are 80 proteins in total.

Show all enzymes and transporters